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Pittsfield, MA accommodations
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288 Lodgings in Pittsfield, MA

Search Lodgings near the Old Town in Pittsfield, MA

Choosing central accommodation in downtown Pittsfield, MA maximizes your time, putting popular museums, historic districts, and local restaurants within walking distance.

Hawksnest: Quiet 2br Apt, Heart Of The Berkshires - Pittsfield, MA
9.7 194 reviews

Hawksnest: Quiet 2br Apt, Heart Of The Berkshires

apartment, Pittsfield
This renovated Pittsfield apartment, conveniently located off Highway 7, provides easy access to Berkshire attractions like Kripalu Center for Yoga & Health, Lenox, and Tanglewood (all within 15 minutes).
The 2-bedroom, 1-bathroom rental offers a private entrance, a screened porch, shared backyard access, and accommodates up to 4 guests with amenities including air conditioning, free internet, and parking.
Downtown Apartment A - Pittsfield, MA
9.9 116 reviews

Downtown Apartment A

apartment, Pittsfield
This Pittsfield apartment is conveniently located in a quiet neighborhood, just 5 minutes from Bousquet Ski Area and close to Jimmy Peak, making it ideal for winter sports enthusiasts. The apartment has received excellent ratings for user experience, location, and cleanliness.
The apartment is a 2-bedroom rental that can accommodate up to 4 guests. It features a full kitchen with a fridge, freezer, and microwave oven, along with air conditioning, parking, and internet access. The apartment is close to Tanglewood, Mass MoCA, hiking trails, and a variety of restaurants, offering easy access to cultural and outdoor activities.
Spacious Historic Home In The Berkshires! - Pittsfield, MA
9.0 1 review

Spacious Historic Home In The Berkshires!

house, Pittsfield
This five-bedroom Pittsfield vacation home is conveniently located 7.6 miles from Tanglewood and 7.8 miles from the Cranwell Spa & Golf Club, offering easy access to area attractions.
The 3,300-square-foot property boasts a fully equipped kitchen, in-house laundry, a fireplace, and accommodates up to 17 guests, perfect for large families or groups visiting the Berkshires.
Spacious 2 Bedroom Downtown Very Nice Area! - Pittsfield, MA
9.6 58 reviews

Spacious 2 Bedroom Downtown Very Nice Area!

apartment, Pittsfield
This Pittsfield apartment rental is centrally located, a 5-minute walk from downtown's main street, offering easy access to numerous cafes, restaurants, shops, and a movie theater.
The two-bedroom, one-bathroom unit comfortably sleeps four guests and includes amenities such as air conditioning, internet, and parking.

Choose the Right Family Lodgings in Pittsfield, MA

These family-friendly lodgings in Pittsfield, MA offer plenty of room and keep city attractions within easy reach; find the perfect fit for your group.

Serene Lenox Hills Cottage - Berkshires - Pittsfield, MA
9.6 45 reviews

Serene Lenox Hills Cottage - Berkshires

cabin, Lenox
Lenox Hills Cottage is a cozy 2-bedroom cottage in the heart of the Berkshires, just minutes from popular attractions like Tanglewood and downtown Lenox. With excellent user, location, and cleanliness ratings, this cabin is a great choice for travelers seeking a comfortable and convenient stay.
The cottage features a wraparound porch for outdoor dining, a screened sunroom with a hammock, an indoor wood-burning fireplace, and a fully equipped kitchen. It can accommodate up to four guests comfortably and offers ample parking space. The surrounding wooded area provides privacy and opportunities for outdoor exploration.
Elmer Estate - Pittsfield, MA
9.8 11 reviews

Elmer Estate

apartment, Pittsfield
This 3-bedroom, 1-bathroom apartment is situated on the Pittsfield/Lenox border, offering a 5-10 minute drive to Pittsfield's shopping, dining, and art venues, as well as nearby ski resorts.
This rental sleeps up to 5 guests and features internet, air conditioning, a kitchen, parking, and two porches with scenic views of the Berkshire Hills.
Richmond Ranch W/ Hot Tub By Evergreen Home - Pittsfield, MA
10 5 reviews

Richmond Ranch W/ Hot Tub By Evergreen Home

apartment, Richmond
This Richmond, Massachusetts farmhouse offers a secluded mountain setting near Hancock Shaker Village and Lenox Mountain Reserve, providing easy access to area attractions.
The 1300-square-foot property features three bedrooms, two bathrooms, and can accommodate six guests, boasting a fully equipped kitchen, jacuzzi, and on-site laundry facilities, plus BBQ and patio areas.
Wildlife Lakeside Cottage;  Views/wildlife - Pittsfield, MA
9.7 383 reviews

Wildlife Lakeside Cottage; Views/wildlife

apartment, Lanesborough
This waterfront vacation home is located in Lanesborough, Massachusetts, just six miles from Mount Greylock State Reservation, St. Mary's of the Assumption Church, and the Crane Museum of Papermaking. The home boasts excellent user, location, and cleanliness ratings, making it a popular choice for travelers.
This comfortable house has three bedrooms, sleeping up to six guests. Enjoy the fully equipped kitchen, a spacious patio, and the peaceful garden, all while taking advantage of the nearby attractions and the breathtaking views from the waterfront.

Frequently Asked Questions about accommodations in Pittsfield, MA

  • What are the top attractions and must-see sites in Pittsfield, MA?

    You definitely want to check out the Berkshire Museum, it has a great collection of art and history. The Clark Art Institute is also a must-see, they have an amazing collection of Impressionist and early modern art, and the grounds are beautiful. And don't forget about the Barrington Stage Company, they put on some great shows throughout the year.
  • What are the best accommodations in Pittsfield, MA?

    Among the accommodations in Pittsfield, MA, Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield are the most popular ones.

  • Which cultural festivals and seasonal events should visitors attend in Pittsfield, MA?

    The biggest event is the 10 Days of Summer festival in July, it's a great way to experience local music and art. You should also check out the Pittsfield Farmers Market on Saturdays, it's a great place to get fresh produce and local crafts. And if you're in town during the fall, you can't miss the foliage, it's absolutely stunning.
  • What are the best accommodations with a pool in Pittsfield, MA?

  • What are the most convenient modes of transportation within Pittsfield, MA?

    Pittsfield is pretty walkable, especially downtown. You can also take the bus, the Berkshire Regional Transit Authority has routes throughout the city. If you're planning on exploring the surrounding area, renting a car is your best bet.
  • What are the best accommodations with a jacuzzi in Pittsfield, MA?

  • What outdoor activities and adventures are popular in and around Pittsfield, MA?

    There's plenty to do outdoors in Pittsfield. You can hike or bike the Appalachian Trail, go kayaking on Lake Onota, or visit the nearby Mount Greylock State Reservation, the highest point in Massachusetts. You can also check out the Taconic Crest Trail, which runs along the Taconic Mountains.
  • What are the best accommodations for families and kids in Pittsfield, MA?

    The best accommodations for families and kids in Pittsfield, MA are Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield.

  • What types of accommodations are available in Pittsfield, MA?

    You can find everything from budget-friendly motels to upscale hotels in Pittsfield. There are also a few bed and breakfasts and vacation rentals available. You can also find some great places to stay in the nearby towns of Lenox and Stockbridge.
  • What are the best pet friendly accommodations in Pittsfield, MA?

    The best pet friendly accommodations in Pittsfield, MA are Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield.

  • When is the best time to visit Pittsfield, MA?

    The best time to visit Pittsfield is in the fall, when the leaves change color. It's also a great time to visit in the summer, when the weather is warm and there are lots of outdoor activities to enjoy. You can find some great deals on accommodations during the shoulder seasons, too.
  • What are the best accommodations with parking in Pittsfield, MA?

    Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield are the best accommodations with parking in Pittsfield, MA.

  • What local dishes and culinary experiences are a must-try in Pittsfield, MA?

    You have to try the Berkshire pork. It's a local specialty, and there are plenty of restaurants in Pittsfield that serve it. You should also check out the local breweries, they're making some really great craft beers. You can also find some great Italian food in Pittsfield, it's a popular cuisine here.
  • In which part of Pittsfield, MA should you consider renting accommodation?

    Downtown Pittsfield is a good choice, it's close to all the action and has a good selection of restaurants and shops. If you're looking for something quieter, you might want to consider staying in the nearby town of Lenox, which is known for its beautiful scenery and charming shops.

Popular destinations

Best Pittsfield, MA accommodation with a kitchen

Modern Gem In The Heart Of Berkshires - Pittsfield, MA
9.9 70 reviews

Modern Gem In The Heart Of Berkshires

apartment, Pittsfield
This Pittsfield apartment is conveniently located near both South and North County attractions, including Mass MoCA, the Clark Institute, and Tanglewood, making it a great base for exploring the Berkshires. The apartment has earned excellent ratings for its cleanliness, location, and user experience.
The apartment features a spacious living and dining area, perfect for relaxing after a day of exploring, and comfortably accommodates up to four guests. Amenities include a screened-in porch, a shared backyard, a well-equipped kitchen, a modern bathroom, driveway parking, and laundry access.
1br Apt, Private Entry, Kitchenette & Fridge - Pittsfield, MA
9.7 6 reviews

1br Apt, Private Entry, Kitchenette & Fridge

apartment, Lenox
This Berkshire district apartment is located 3 minutes from Tanglewood and 4 minutes from Kripalu Yoga Center, offering a prime location for accessing local highlights.
This one-bedroom, one-bathroom unit accommodates up to three guests and includes internet, a kitchen with a fridge and microwave, and parking, providing a serene environment for relaxation and visiting nurses.
Lake Views & Dock Access - Pittsfield Cottage! - Pittsfield, MA
9.4 6 reviews

Lake Views & Dock Access - Pittsfield Cottage!

cottage, Lanesborough
This Lanesborough lakeside home is located near Pontoosuc Lake, just two miles from Balanced Rock State Park, five miles from Pittsfield State Forest, and eight miles from Jiminy Peak Mountain Resort. This five-bedroom, two-bathroom vacation rental boasts 2,000 square feet of space, sleeps up to eight guests, includes a private boat dock, kayaks, canoes, and a pedal boat, and offers amenities such as WiFi, central air conditioning, and a gas grill.
Renovated Pittsfield Colonial By Evergreen Home - Pittsfield, MA
9.9 101 reviews

Renovated Pittsfield Colonial By Evergreen Home

apartment, Pittsfield
This Pittsfield apartment is in the heart of the Berkshires, surrounded by museums, theaters, and hiking trails. It has excellent user, location, and cleanliness ratings.
The apartment has 4 bedrooms, 3 bathrooms, and a bonus room, with a floor area of 3900 square feet. It can accommodate up to 12 guests. The kitchen has new appliances, and there's a large deck overlooking a private backyard and woods. Other amenities include Wi-Fi, a washer and dryer, a fitness center, and parking.

Neighborhoods and points of interest in Pittsfield, MA

Best Pittsfield, MA accommodation with parking

Berkshire Mountain Lodge - Pittsfield, MA
8.9 1792 reviews

Berkshire Mountain Lodge

house, Pittsfield
Located in Pittsfield, this chalet is close to Guido's Marketplace and within 3 miles of attractions such as Bousquet Ski Area and Housatonic River. With a very good user rating and an excellent location rating, this chalet offers a comfortable stay for travelers.
The chalet features one bedroom and one bathroom, and includes a kitchen with a fridge, microwave oven, and dishwasher. Guests can enjoy amenities such as air conditioning, a swimming pool, a Jacuzzi, a garden, a sauna, a spa, a concierge, a restaurant, a bar, a fitness center, and parking.
Marie's Place - Pittsfield, MA
9.8 328 reviews

Marie's Place

apartment, Pittsfield
This apartment is located in Pittsfield, just a short drive from the city's cultural attractions like the Berkshire Museum, Colonial Theater, and Barrington Stage Company. It has excellent user, location, and cleanliness ratings, making it a great choice for travelers. The apartment is fully furnished and comfortably accommodates up to four guests. You'll enjoy convenient on-site laundry facilities, off-street parking, and access to the yard and parking area, making your stay hassle-free.
Relaxing Berkshire Getaway - Pittsfield, MA
9.9 78 reviews

Relaxing Berkshire Getaway

apartment, Pittsfield
This Pittsfield vacation rental is located in a quiet residential area, just a short walk from Pontoosuc Lake and a quick drive to hiking trails, biking paths, and shopping. The property has received excellent ratings for its cleanliness, location, and overall experience.
The home has two bedrooms with queen beds, a living room with a pull-out bed, and a renovated bathroom, comfortably accommodating up to six guests. Enjoy modern amenities like smart TVs, a gas fireplace, and a washer and dryer, plus outdoor spaces with decks, a gas grill, and a fire table.
The Oliver Wendell Holmes Guesthouse @ Holmesdale - Pittsfield, MA
9.6 105 reviews

The Oliver Wendell Holmes Guesthouse @ Holmesdale

apartment, Pittsfield
Historic Holmesdale Cottage is situated on 16 acres of a private estate on the Pittsfield/Lenox border, offering tranquility amidst the Berkshires. With excellent user, location, and cleanliness ratings, this one-bedroom, one-bathroom cottage accommodates up to four guests, featuring a king-size bed and a spiral staircase.
Guests enjoy access to a pool, tennis court, and reflecting pond, along with modern conveniences like central AC/heat, high-end appliances, and a king-size iComfort mattress with luxury linens. The cottage retains original details like wood floors and a fireplace, while offering stunning views of the Berkshire mountains.

Best Pittsfield, MA lodging with a pool

Among the 288 accommodations in Pittsfield, MA, here are the 3 best ones with a pool

Lenox Grand Colonial With Pool By Evergreen Home - Pittsfield, MA
10 3 reviews

Lenox Grand Colonial With Pool By Evergreen Home

apartment, Lenox
Grand Berkshire Manor By Evergreen Home - Pittsfield, MA
No reviews

Grand Berkshire Manor By Evergreen Home

apartment, Pittsfield
Architectural Lenox Escape W/pool And Sauna - Pittsfield, MA
10 8 reviews

Architectural Lenox Escape W/pool And Sauna

apartment, Lenox

Browse 5-Star Accommodations in Pittsfield, MA

Comfort and a prime location define these luxury lodgings in Pittsfield, MA, each hand-selected with your total relaxation in mind.

Centrally Located In The Berkshires - Cozy Bungalow In Se Pittsfield! - Pittsfield, MA
10 5 reviews

Centrally Located In The Berkshires - Cozy Bungalow In Se Pittsfield!

apartment, Pittsfield

Top-Rated Pet-Friendly Lodgings in Pittsfield, MA

Traveling with a pet to Pittsfield, MA is effortless when your lodging is equipped with nearby dog parks and city walks right on the doorstep.

Charming Apartment In Central Pittsfield - Pittsfield, MA
9.2 82 reviews

Charming Apartment In Central Pittsfield

apartment, Pittsfield
Explore The Berkshires From This Charming Home. - Pittsfield, MA
9.8 37 reviews

Explore The Berkshires From This Charming Home.

apartment, Pittsfield
Hidden Oasis In The Mountains By Evergreen Home - Pittsfield, MA
9.9 172 reviews

Hidden Oasis In The Mountains By Evergreen Home

apartment, Pittsfield
New Built - Split Level House In The Berkshires - Pittsfield, MA
10 4 reviews

New Built - Split Level House In The Berkshires

apartment, Lanesborough
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